Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614022232/fm3027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614022232/fm3027Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614022232/fm3027Isup3.cml |
CCDC reference: 1028136
As part of our continued interest in the multicomponent synthesis of compounds with the pyrrolidinedione skeleton, some of which have reportedly demonstrated promising antimicrobial properties (Gein et al., 2007), we report here the structure of 4-(3-azaniumylpropyl)morpholin-4-ium chloride hydrogen oxalate, (I), an organic–inorganic mixed salt formed as a by-product during the synthesis of the hydrochloride salt of the pyrrolidinone carbaldehyde parent compound, 4-(benzofuran-2-carbonyl)-5-[4-(tert-butyl)phenyl]-3-hydroxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one, (II). Mixed salts have many practical and potential applications in the fields of magnetism and electric conductors, energy storage, solar energy conversion, as well as catalysis and the biomedical field (Hill & Prossner-McCartha, 1995; Mizuno & Misomo, 1998; Gouzerh & Proust, 1998; Proust et al., 1993; Zhuang et al., 2010; Huang et al., 2009; Zhou & Yu, 2012; You et al., 2006). The crystal packing of such compounds is often characterized by extensive hydrogen bonding and charge-assisted intermolecular interactions (Brammer et al., 2002; Huang et al., 2009).
Methyl (2Z)-4-(1-benzofuran-2-yl)-2-hydroxy-4-oxobut-2-enoate (0.200 g, 0.816 mmol) was dissolved in 1,4-dioxane (5 ml). One molar equivalent of 4-(3-aminopropyl)morpholine (0.816 mmol, 0.119 ml) was added to the dioxane mixture, resulting in a yellow precipitate forming upon addition. One molar equivalent of tert-butylbenzaldehyde (0.816 mmol, 0.137 ml) was added to the mixture and stirred at room temperature for 5 min. 4-(Benzofuran-2-carbonyl)-5-[4-(tert-butyl)phenyl]-3-hydroxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one was isolated as a yellow powder (0.579 mmol, 0.291 g; 71% yield) and dried in vacuo. Subsequently, the dried powder (0.050 g, 0.093 mmol) was dissolved in dry methanol (2.5 ml). One drop of 15% HCl was added to this solution which was agitated to cause mixing. 4-(Benzofuran-2-carbonyl)-5-(4-tert-butylphenyl)-3-hydroxy-1-[3-(morpholin-4-yl)propyl]-1H-pyrrol-2(5H)-one hydrochloride salt, (II), precipitated out of the solution and was isolated as an off-white powder (yield 0.0716 mmol, 0.039 g, 77%), while colourless crystals of the title salt, (I), crystallized out of the methanolic solution as a by-product (<5% yield).
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in idealized positions and were allowed to ride on their parent atoms, with C—H = 0.97 Å, N—H = 0.89 Å and O—H = 0.82 Å, and with Uiso(H) = 1.5Ueq(C,O) for primary ammonium and hydroxy groups, and 1.2Ueq(C) otherwise.
The asymmetric unit of salt (I) consists of one 4-(3-azaniumylpropyl)morpholin-4-ium dication, doubly protonated at atoms N1 and N2, counter-balanced by two different anions, viz. a hydrogen oxalate anion and a chloride anion (Fig. 1). The morpholine ring assumes a low-energy chair conformation, with the azaniumylpropyl side chain in an antiperiplanar (anti or trans) conformation [the C5—C6—C7—N2 torsion angle is 173.04 (8)°]. All other bond lengths and angles in the 4-(3-azaniumylpropyl)morpholin-4-ium dication fall within expected ranges. Typical variations in the C—O bond lengths can be observed for the hydrogen oxalate anion; whereas the short bond distances of the charged carboxylate end C8—O2 and C8—O3 [1.2474 (12) and 1.2571 (14) Å, respectively] indicates a delocalization of charge across both C—O bonds, the longer bond length observed for C9—O5 [1.3113 (14) Å] and the short length for C9—O4 [1.2150 (13) Å] is consistent with a carboxylic acid group containing distinct C═O and C—OH bonds.
Fig. 2 shows the crystal packing along the crystallographic b axis in the form of layers. Hydrogen oxalate anions are sandwiched by the 3-(morpholin-4-yl)propan-1-aminium cations, which are in turn separated by the chloride anions, as viewed in the ac plane. The sandwiched hydrogen oxalate anions interact through a number of different hydrogen bonds, as shown in Fig. 3. The individual sandwich layers are connected through Couloumbic interactions involving the chloride anions.
The extensive network of intermolecular interactions displayed in the structure of compound (I) can be described by a combination of graph-set symbols (Bernstein et al., 1995). Atom H8C is a triple donor to O1iii, O3iv and O4iv, with the H8C···O4iv distance shorter than the corresponding H8C···O3iv distance (see Table 2 for hydrogen-bond geometry and symmetry codes; Fig. 3). This results in a cyclic R22(5) motif.
Atoms H8A and H8B link the cations in a head-to-head manner through Cl1, resulting in chains that spiral down the crystallographic b axis (Fig 4). Furthermore, an additional head-to-tail pairing can be observed for the cations through the weak hydrogen bonding of H8C···O1iii. The H8C···O1iii interaction connects the 4-(3-azaniumylpropyl)morpholin-4-ium dications in a head-to-tail manner, forming C(9) chains that run diagonally along the ab face (Fig. 5a). Furthermore, the hydrogen oxalate anions are interconnected via O—H···O hydrogen bonds, forming head-to-tail C(5) chains along the crystallographic b axis (Fig. 5b). Additional intermolecular C—H···Cl interactions formed between H3A and the chloride counter-ion result in chains that spiral down the crystallographic b axis (Fig. 4). Furthermore, atom O2 is involved in interactions with N1—H1 and H6A, resulting in a ring denoted R21(6), while three additional hydrogen bonds (N—H1···O2, O5—H5···O3i and C3—H3B···.O2i) result in a third ring, denoted R33(12) in graph-set notation (Fig. 3). Due to the fact that atom O5 is a double donor to H3B and H1, several smaller rings can be identified that are contained within ring R33(13). These include R33(9) formed by N—H1···O5, O5—H5···O3i and O2i···C3—H3B; R22(8) formed by N—H1···O2 and O5···C3—H3B; and R21(5) formed by N—H1···O5 and O5···C3—H3B, as well as R12(5) formed by (N)H1···O2 and O5···(N)H1 and lastly R23(6) formed by H3B···O5, O5—H5···O3i and O2i···H3B. The C—H···O, O—H···O and N—H···O hydrogen-bond distances vary between 1.73 and 2.60 Å, while the N—H···Cl and C—H···Cl interaction distances vary between 2.27 and 2.71 Å. All interactions in the structure are shorter than the sum of the van der Waals radii of the interacting atoms, where r(O) + r(H) = 2.72 Å and r(Cl) + r(H) = 3.00 Å, respectively (Mantina et al. 2009). In addition, the hydrogen-bond angles range between 133 and 172°, with the exception of N1—H1···O5 [123 (2)°], N2—H8C···O1iii (117°) and the nonclassical C3—H3B···O5 (114°). Most of the interactions observed in the structure therefore correspond well to what is considered strong hydrogen bonding, thereby contributing to the stability of the structure.
Residual electron density is found on a twofold axis near atoms H6B (2.33 Å), H2A (2.38 Å) and Cl1 (2.89 Å). Probing of the electron density showed it to be well positioned to be a water molecule with possible H2O—H hydrogen bonding to H6B and H2A, as well as showing a possible O—H···Cl short interaction. Refining of the residual electron density as an O atom, however, indicated that the occupancy would be very low as well as having huge uncertainty in the H-atom placement due to lack of electron density. Taking into account the low occupancy of any atom placed in this position, it is plausible that the residual electron density is an artefact in the data.
Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006), DIAMOND (Brandenburg, 2006) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C7H18N2O2+·C2HO4−·Cl− | F(000) = 1152 |
Mr = 270.71 | Dx = 1.430 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 9809 reflections |
a = 18.949 (5) Å | θ = 2.4–28.3° |
b = 5.685 (5) Å | µ = 0.32 mm−1 |
c = 24.783 (5) Å | T = 100 K |
β = 109.575 (5)° | Block, colourless |
V = 2515 (2) Å3 | 0.32 × 0.24 × 0.14 mm |
Z = 8 |
Bruker APEX-II CCD diffractometer | 2954 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 28.4°, θmin = 1.7° |
ϕ and ω scans | h = −25→25 |
46562 measured reflections | k = −7→7 |
3150 independent reflections | l = −33→33 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0441P)2 + 2.538P] where P = (Fo2 + 2Fc2)/3 |
3150 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C7H18N2O2+·C2HO4−·Cl− | V = 2515 (2) Å3 |
Mr = 270.71 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.949 (5) Å | µ = 0.32 mm−1 |
b = 5.685 (5) Å | T = 100 K |
c = 24.783 (5) Å | 0.32 × 0.24 × 0.14 mm |
β = 109.575 (5)° |
Bruker APEX-II CCD diffractometer | 2954 reflections with I > 2σ(I) |
46562 measured reflections | Rint = 0.033 |
3150 independent reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.26 e Å−3 |
3150 reflections | Δρmin = −0.23 e Å−3 |
154 parameters |
Experimental. Crystals of [C7H18N2O]2+·C2HO4-·Cl-, (I), were grown by slow evaporation from a saturated methanolic solution of 4-(benzofuran-2-carbonyl)-5- (4-(tert-butyl)phenyl)-3-hydroxy-1-(3-morpholinopropyl)-1H-pyrrol-2(5H)-one (II), acidified with hydrochloric acid. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Crystal evaluation and data collection were performed on a Bruker APEXII CCD diffractometer with Mo Kα (λ = 0.71069 Å) radiation and a diffractometer-to-crystal distance of 4.00 cm, at the Department of Chemistry, Auckland Park campus of the University of Johannesburg, South Africa. The initial cell matrix was obtained from two series of scans at different starting angles. Each series consisted of 12 frames collected at intervals of 0.5° in a 6° range with the exposure time of 10 s per frame. The reflections were successfully indexed by an automated indexing routine built in the APEXII program suite (APEX2 and SAINT; Bruker, 2012). The final cell constants were calculated from a set of 3150 strong reflections from the actual data collection. The data were collected by using the full-sphere data collection routine to survey the reciprocal space to the extent of a full sphere to a resolution of 0.75 Å. Data were harvested by collecting frames at intervals of 0.5° scans in ω and ϕ, with exposure times of 20 s per frame. These highly redundant data sets were corrected for Lorentz and polarization effects. The absorption correction was based on fitting a function to the empirical transmission surface as sampled by multiple equivalent measurements (SADABS; Bruker, 2012). The systematic absences in the diffraction data were uniquely consistent for the space group C2/c that yielded chemically reasonable and computationally stable refinement results. A successful solution by direct methods (SHELXS97; Sheldrick, 2008) provided all non-H atoms from the E-map. All non-H atoms were refined with anisotropic displacement parameters. The final least-squares refinement of parameters against data resulted in residuals R (based on F2 for I ≥ 2σ) and wR (based on F2 for all data) values unique to the crystal. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.06713 (6) | −0.09471 (18) | 0.61326 (5) | 0.0148 (2) | |
H1A | 0.1097 | −0.1902 | 0.6347 | 0.018* | |
H1B | 0.0384 | −0.1826 | 0.5795 | 0.018* | |
C2 | 0.01853 (6) | −0.04815 (18) | 0.65010 (4) | 0.01290 (19) | |
H2A | 0.0008 | −0.1958 | 0.6604 | 0.015* | |
H2B | 0.0476 | 0.0319 | 0.6850 | 0.015* | |
C3 | −0.01715 (6) | 0.32481 (17) | 0.60042 (4) | 0.01205 (19) | |
H3A | 0.0121 | 0.4099 | 0.6345 | 0.014* | |
H3B | −0.0583 | 0.4243 | 0.5785 | 0.014* | |
C4 | 0.03162 (6) | 0.26306 (18) | 0.56479 (5) | 0.0143 (2) | |
H4A | 0.0017 | 0.1812 | 0.5304 | 0.017* | |
H4B | 0.0504 | 0.4065 | 0.5533 | 0.017* | |
C5 | −0.10022 (6) | 0.15209 (18) | 0.64870 (4) | 0.01321 (19) | |
H5A | −0.1368 | 0.2676 | 0.6277 | 0.016* | |
H5B | −0.0728 | 0.2174 | 0.6860 | 0.016* | |
C6 | −0.14042 (6) | −0.07162 (19) | 0.65617 (5) | 0.0148 (2) | |
H6A | −0.1570 | −0.1585 | 0.6204 | 0.018* | |
H6B | −0.1061 | −0.1707 | 0.6851 | 0.018* | |
C7 | −0.20762 (6) | −0.01054 (18) | 0.67407 (5) | 0.0142 (2) | |
H7A | −0.1907 | 0.0587 | 0.7120 | 0.017* | |
H7B | −0.2390 | 0.1033 | 0.6476 | 0.017* | |
N1 | −0.04685 (5) | 0.10181 (15) | 0.61690 (4) | 0.01050 (17) | |
H1 | −0.0725 | 0.0236 | 0.5842 | 0.013* | |
N2 | −0.25144 (5) | −0.22804 (16) | 0.67412 (4) | 0.01376 (18) | |
H8A | −0.2908 | −0.1926 | 0.6845 | 0.021* | |
H8B | −0.2226 | −0.3313 | 0.6987 | 0.021* | |
H8C | −0.2672 | −0.2902 | 0.6391 | 0.021* | |
O1 | 0.09326 (4) | 0.11814 (13) | 0.59603 (3) | 0.01537 (16) | |
C8 | −0.16604 (6) | −0.21555 (17) | 0.48876 (4) | 0.01075 (18) | |
C9 | −0.19432 (6) | 0.03209 (17) | 0.46434 (4) | 0.01088 (19) | |
O2 | −0.11121 (4) | −0.22588 (13) | 0.53391 (3) | 0.01368 (15) | |
O3 | −0.20129 (4) | −0.38517 (13) | 0.45938 (3) | 0.01467 (16) | |
O4 | −0.24188 (4) | 0.05627 (13) | 0.41753 (3) | 0.01467 (16) | |
O5 | −0.16082 (4) | 0.20390 (13) | 0.49869 (3) | 0.01502 (16) | |
H5 | −0.1775 | 0.3303 | 0.4840 | 0.023* | |
Cl1 | −0.367263 (14) | −0.01834 (4) | 0.729512 (10) | 0.01563 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0145 (5) | 0.0119 (4) | 0.0192 (5) | 0.0021 (4) | 0.0073 (4) | 0.0019 (4) |
C2 | 0.0116 (4) | 0.0125 (4) | 0.0138 (5) | 0.0029 (3) | 0.0032 (4) | 0.0025 (4) |
C3 | 0.0128 (4) | 0.0093 (4) | 0.0140 (4) | −0.0003 (3) | 0.0044 (4) | 0.0005 (3) |
C4 | 0.0151 (5) | 0.0131 (4) | 0.0156 (5) | 0.0013 (4) | 0.0061 (4) | 0.0021 (4) |
C5 | 0.0124 (4) | 0.0140 (4) | 0.0150 (5) | 0.0011 (4) | 0.0068 (4) | −0.0008 (4) |
C6 | 0.0141 (5) | 0.0142 (5) | 0.0178 (5) | −0.0002 (4) | 0.0076 (4) | 0.0003 (4) |
C7 | 0.0137 (5) | 0.0139 (5) | 0.0166 (5) | −0.0012 (4) | 0.0070 (4) | −0.0006 (4) |
N1 | 0.0099 (4) | 0.0101 (4) | 0.0110 (4) | 0.0004 (3) | 0.0029 (3) | 0.0000 (3) |
N2 | 0.0121 (4) | 0.0160 (4) | 0.0129 (4) | −0.0013 (3) | 0.0039 (3) | −0.0006 (3) |
O1 | 0.0125 (3) | 0.0139 (3) | 0.0210 (4) | 0.0012 (3) | 0.0071 (3) | 0.0027 (3) |
C8 | 0.0117 (4) | 0.0098 (4) | 0.0115 (4) | 0.0011 (3) | 0.0049 (3) | 0.0007 (3) |
C9 | 0.0106 (4) | 0.0099 (4) | 0.0125 (4) | 0.0006 (3) | 0.0044 (3) | −0.0001 (3) |
O2 | 0.0144 (3) | 0.0116 (3) | 0.0122 (3) | 0.0010 (3) | 0.0007 (3) | 0.0003 (3) |
O3 | 0.0162 (4) | 0.0101 (3) | 0.0149 (3) | −0.0007 (3) | 0.0013 (3) | −0.0006 (3) |
O4 | 0.0151 (4) | 0.0128 (3) | 0.0132 (3) | 0.0018 (3) | 0.0009 (3) | 0.0000 (3) |
O5 | 0.0178 (4) | 0.0079 (3) | 0.0152 (4) | 0.0007 (3) | 0.0000 (3) | −0.0003 (3) |
Cl1 | 0.01616 (14) | 0.01693 (13) | 0.01260 (13) | 0.00007 (8) | 0.00323 (10) | −0.00131 (8) |
C1—O1 | 1.4260 (15) | C5—H5B | 0.9700 |
C1—C2 | 1.5215 (15) | C6—C7 | 1.5224 (15) |
C1—H1A | 0.9700 | C6—H6A | 0.9700 |
C1—H1B | 0.9700 | C6—H6B | 0.9700 |
C2—N1 | 1.5018 (13) | C7—N2 | 1.4897 (16) |
C2—H2A | 0.9700 | C7—H7A | 0.9700 |
C2—H2B | 0.9700 | C7—H7B | 0.9700 |
C3—N1 | 1.4983 (16) | N1—H1 | 0.9100 |
C3—C4 | 1.5177 (14) | N2—H8A | 0.8900 |
C3—H3A | 0.9700 | N2—H8B | 0.8900 |
C3—H3B | 0.9700 | N2—H8C | 0.8900 |
C4—O1 | 1.4270 (13) | C8—O2 | 1.2474 (12) |
C4—H4A | 0.9700 | C8—O3 | 1.2570 (14) |
C4—H4B | 0.9700 | C8—C9 | 1.5550 (18) |
C5—N1 | 1.5030 (13) | C9—O4 | 1.2150 (13) |
C5—C6 | 1.5253 (17) | C9—O5 | 1.3114 (14) |
C5—H5A | 0.9700 | O5—H5 | 0.8200 |
O1—C1—C2 | 111.88 (9) | C7—C6—H6A | 109.6 |
O1—C1—H1A | 109.2 | C5—C6—H6A | 109.6 |
C2—C1—H1A | 109.2 | C7—C6—H6B | 109.6 |
O1—C1—H1B | 109.2 | C5—C6—H6B | 109.6 |
C2—C1—H1B | 109.2 | H6A—C6—H6B | 108.1 |
H1A—C1—H1B | 107.9 | N2—C7—C6 | 109.38 (9) |
N1—C2—C1 | 108.91 (8) | N2—C7—H7A | 109.8 |
N1—C2—H2A | 109.9 | C6—C7—H7A | 109.8 |
C1—C2—H2A | 109.9 | N2—C7—H7B | 109.8 |
N1—C2—H2B | 109.9 | C6—C7—H7B | 109.8 |
C1—C2—H2B | 109.9 | H7A—C7—H7B | 108.2 |
H2A—C2—H2B | 108.3 | C3—N1—C2 | 108.26 (8) |
N1—C3—C4 | 108.69 (9) | C3—N1—C5 | 111.23 (8) |
N1—C3—H3A | 110.0 | C2—N1—C5 | 113.41 (8) |
C4—C3—H3A | 110.0 | C3—N1—H1 | 107.9 |
N1—C3—H3B | 110.0 | C2—N1—H1 | 107.9 |
C4—C3—H3B | 110.0 | C5—N1—H1 | 107.9 |
H3A—C3—H3B | 108.3 | C7—N2—H8A | 109.5 |
O1—C4—C3 | 111.42 (9) | C7—N2—H8B | 109.5 |
O1—C4—H4A | 109.3 | H8A—N2—H8B | 109.5 |
C3—C4—H4A | 109.3 | C7—N2—H8C | 109.5 |
O1—C4—H4B | 109.3 | H8A—N2—H8C | 109.5 |
C3—C4—H4B | 109.3 | H8B—N2—H8C | 109.5 |
H4A—C4—H4B | 108.0 | C1—O1—C4 | 110.43 (9) |
N1—C5—C6 | 110.86 (9) | O2—C8—O3 | 127.20 (10) |
N1—C5—H5A | 109.5 | O2—C8—C9 | 117.81 (9) |
C6—C5—H5A | 109.5 | O3—C8—C9 | 114.97 (10) |
N1—C5—H5B | 109.5 | O4—C9—O5 | 125.34 (10) |
C6—C5—H5B | 109.5 | O4—C9—C8 | 121.51 (9) |
H5A—C5—H5B | 108.1 | O5—C9—C8 | 113.14 (9) |
C7—C6—C5 | 110.22 (9) | C9—O5—H5 | 109.5 |
O1—C1—C2—N1 | 58.32 (11) | C6—C5—N1—C3 | 170.13 (8) |
N1—C3—C4—O1 | −60.11 (11) | C6—C5—N1—C2 | −67.56 (11) |
N1—C5—C6—C7 | −165.38 (8) | C2—C1—O1—C4 | −58.45 (11) |
C5—C6—C7—N2 | 173.05 (8) | C3—C4—O1—C1 | 59.29 (11) |
C4—C3—N1—C2 | 58.92 (10) | O2—C8—C9—O4 | 171.81 (10) |
C4—C3—N1—C5 | −175.84 (8) | O3—C8—C9—O4 | −7.03 (14) |
C1—C2—N1—C3 | −58.00 (10) | O2—C8—C9—O5 | −7.05 (13) |
C1—C2—N1—C5 | 178.06 (8) | O3—C8—C9—O5 | 174.11 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.91 | 1.87 | 2.7400 (16) | 160 |
N1—H1···O5 | 0.91 | 2.44 | 3.0568 (12) | 125 |
N2—H8A···Cl1 | 0.89 | 2.32 | 3.1846 (11) | 162 |
N2—H8B···Cl1i | 0.89 | 2.27 | 3.1445 (13) | 166 |
N2—H8C···O4ii | 0.89 | 2.11 | 2.9093 (16) | 149 |
N2—H8C···O3ii | 0.89 | 2.52 | 3.1901 (13) | 133 |
N2—H8C···O1iii | 0.89 | 2.55 | 3.0583 (13) | 117 |
O5—H5···O3iv | 0.82 | 1.73 | 2.548 (2) | 172 |
C3—H3A···Cl1v | 0.97 | 2.71 | 3.6067 (12) | 154 |
C3—H3B···O2iv | 0.97 | 2.33 | 3.233 (2) | 154 |
C3—H3B···O5 | 0.97 | 2.58 | 3.1050 (14) | 114 |
C5—H5A···O4vi | 0.97 | 2.41 | 3.3323 (16) | 158 |
C6—H6A···O2 | 0.97 | 2.60 | 3.3733 (15) | 137 |
C7—H7B···O4vi | 0.97 | 2.47 | 3.359 (2) | 153 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) −x−1/2, −y−1/2, −z+1; (iii) x−1/2, y−1/2, z; (iv) x, y+1, z; (v) x+1/2, y+1/2, z; (vi) −x−1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C7H18N2O2+·C2HO4−·Cl− |
Mr | 270.71 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 100 |
a, b, c (Å) | 18.949 (5), 5.685 (5), 24.783 (5) |
β (°) | 109.575 (5) |
V (Å3) | 2515 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.32 × 0.24 × 0.14 |
Data collection | |
Diffractometer | Bruker APEX-II CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 46562, 3150, 2954 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.080, 1.03 |
No. of reflections | 3150 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.26, −0.23 |
Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006), DIAMOND (Brandenburg, 2006) and ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.91 | 1.87 | 2.7400 (16) | 159.8 |
N1—H1···O5 | 0.91 | 2.44 | 3.0568 (12) | 125.1 |
N2—H8A···Cl1 | 0.89 | 2.32 | 3.1846 (11) | 162.4 |
N2—H8B···Cl1i | 0.89 | 2.27 | 3.1445 (13) | 166.4 |
N2—H8C···O4ii | 0.89 | 2.11 | 2.9093 (16) | 149.0 |
N2—H8C···O3ii | 0.89 | 2.52 | 3.1901 (13) | 132.9 |
N2—H8C···O1iii | 0.89 | 2.55 | 3.0583 (13) | 116.8 |
O5—H5···O3iv | 0.82 | 1.73 | 2.548 (2) | 171.9 |
C3—H3A···Cl1v | 0.97 | 2.71 | 3.6067 (12) | 154.4 |
C3—H3B···O2iv | 0.97 | 2.33 | 3.233 (2) | 154.2 |
C3—H3B···O5 | 0.97 | 2.58 | 3.1050 (14) | 113.8 |
C5—H5A···O4vi | 0.97 | 2.41 | 3.3323 (16) | 158.3 |
C6—H6A···O2 | 0.97 | 2.60 | 3.3733 (15) | 137.2 |
C7—H7B···O4vi | 0.97 | 2.47 | 3.359 (2) | 152.6 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) −x−1/2, −y−1/2, −z+1; (iii) x−1/2, y−1/2, z; (iv) x, y+1, z; (v) x+1/2, y+1/2, z; (vi) −x−1/2, −y+1/2, −z+1. |